Antiseptic soap composition



United States Patent ANTISEPTIC SOAP COMPOSITIDN David J. Beaver, Richmond Heights, Roland S. Shumard,

Brentwood, and Paul J. Stofiel, Florissant, Mo., assignors to Monsanto Chemical Company, St. Louis, Mo., a corporation of Delaware No Drawing. Application September 28, 1953, Serial No. 382,831

4 Claims. (Cl. 252-107) This invention relates to new and useful compositions of matter. More particularly this invention relates to tris-phenols of the general formula on 0H 0H CH OH NO: NO:

where X is a halogen atom.

The new compounds have been found to have antiseptic properties and to be particularly useful in detergent soap compositions.

As illustrative of the preparation of the new compounds of this invention is the following:

Example I Approximately 18.7 parts by weight of 2-hydroxy-5- nitrobenzyl chloride, approximately 6.4 parts by weight of p-chlorophenol, approximately 50 parts by weight of glacial acetic acid and approximately 5 parts by weight of cone. sulfuric acid are intimately mixed. The mixture so obtained is heated to about 90 C. and held at that temperature overnight with constant agitation. Upon cooling 2. grey-white crystalline mass separates. The cooled reaction mass is filtered. The filter cake is washed with water and then recrystallized from toluene. The recrystallized product is a grey-White crystalline solid having a melting point of 273-274 C. and identified as 4-chloro-a,a'-bis(5-nitro-2-hydroxy-phenyl)-2,6-xylenol.

Example 11 Employing the procedure of Example I but replacing p-chlorophenol with an equimolecular proportion of pbromophenol there is obtained 4-bromo-a,a'-bis(5-nitro- 2-hydroxy-phenyl) -2,6-xylenol.

As illustrative of the utility of the new compounds of this invention 4 chloro 01,0! bis(5-nitro-2-hydroxyphenyl) -2,6-Xylenol was compounded in an Ivory brand neutral white high grade tallow soap to form a 2% by weight composition. Aliquots were added to a nutrient agar medium so as to give concentrations of 1.25 p. p. m., 2.5 p. p. m., 5 p. p. m. and 10 p. p. III. of 4- chloro-a,a-bis (5-nitro-2-hydroxy-phenyl) -2,6-xylenol in the nutrient agar. The agar in each case was then streaked with a 24 hour culture of Staphylococci aureus of standard resistance. After an incubation period of 72 hours at 37 C. in each case no growth was observed.

The new compounds are readily incorporated in a detergent soap whether (the soap) be liquid or solid. They, also, remain permanently in the detergent composition and do not afliect the lathering, cleansing or physical properties of the detergent soap. Relatively small amounts of the tris-phenols of this invention in a detergent composition have been found to yield efiicient antiseptic detergent compositions. While amounts in the range of 13% by weight based upon the detergent soap are preferred amounts in the range of 05-10% by weight may be employed where desired.

The term soap or detergent soap as employed herein is employed in its popular or ordinary meaning, i. e., cleansing compositions prepared from an alkali metal compound such as potassium or sodium hydroxide and a fat or fatty acid, both saturated and unsaturated.

While the invention has been described in detail with respect to certain embodiments it is not so limited and it is to be understood that modifications and variations obvious to those skilled in the art may be made without departing from the spirit or scope of this invention.

What is claimed is:

1. As a new compound a 4-ha10-a,u.'-biS(S-IfilI'O-Z- hydroxy-phenyl) -2,6-xylenol.

2. 4 chloro (2,11 bis(5 nitro 2 hydroxyphenyl) -2,6-xylenol.

3. 4 bromo 0:,a' bis(5 nitro 2 hydroXy-phenyD- 2,6-xylenol.

4. An antiseptic detergent composition comprising the combination of a detergent soap and 0.5 to 10% by weight based upon the detergent coap of a compound of claim 1.

OTHER REFERENCES Jour. Amer. Chem. soc. vol. 75 (Nov. 20, 1953), pages 5579-81. 

1. AS A NEW COMPOUND A 4-HALO-A,A''-BIS(5-NITRO-2HYDROXY-PHENYL)-2,6-XYLENOL.
 4. AN ANTISEPTIC DETERGENT COMPOSITION COMPRISING THE COMBINATION OF A DETERGENT SOAP AND 0.5 TO 10% BY WEIGHT BASED UPON THE DETERGENT SOAP OF A COMPOUND OF CLAIM
 1. 